Iodine → 3-tert-Butyl-1,2-thiazol-5-amine

Participants

Reaction Steps

To a stirred solution of (Z)-3-amino-4,4-dimethyl-pent-2-enethioic acid amide (8.3 g, 525 mmol) and potassium carbonate (14.4 g, 105 mmol) in 140 mL of diethyl ether is added a solution of iodine (13.2 g, 52.5 mmol) in 20 mL of diethyl ether at reflux. The mixture is refluxed for 2 h and cooled. Water is added and the layers separated. The organic layer is washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude mixture is purified by flash chromatography to afford title compound in 53% yield. ESI m/z 157=MH+

Provenance & Evidence